How should startups look to sell to CIOs?

Startups should understand the pain points faced by CIOs - for example, challenges such as maintenance cost, the cost of fixing bugs, reputation cost, or any others. Connect on the pain point first, build trust, then sell.

One of the biggest mistakes I see in sales, from a startup or otherwise, is the trap of thinking the conversation is about your company and the “features” of your product or solution. All that fancy credibility and capability means nothing until connected to a problem the buyer truly needs to solve. 

So when approaching that CIO, make the conversation center around their needs. 

1. Speak specifically to the problem they have. As others have said, this means doing your homework and understanding their situation. 

2. Make them see and feel what it’s like for that problem to be solved. 

3. Now you can connect the dots to your solution. How is your solution the obvious choice for solving that problem and producing those outcomes. 

4. And finally, why should they believe you? 

Many people approach this exactly backwards. 

1) clear value proposition - time to market, differentiator, efficiency
2) support for the start-up - financing and the long term viability of the idea
3) founder and team credentials in technology, domain
4) market positioning 

First look at your potential client pool and get a good idea of what the primary expectations are. Second is to set reasonable achievable goals that you are certain not only can be net but exceeded with ease and efficiency 

Do some research on the company
Do some research on me
Show me how your product adds value to MY enterprise in the first 5 minutes of the conversation
Respect my time
Do NOT request a connection in LinkedIn and then jump straight into the sales pitch on your next message
Respect my decision, if I say I am not interested then acept that